Chapter 22: Q29E (page 752)
Using curved arrows, propose a mechanism for the following reaction, one of the steps in the biosynthesis of the amino acid tyrosine.

Short Answer

Mechanism
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Chapter 22: Q29E (page 752)
Using curved arrows, propose a mechanism for the following reaction, one of the steps in the biosynthesis of the amino acid tyrosine.


Mechanism
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Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case.
(a)Ethyl pentanoate (b)Ethyl 3-methylbutanoate
(c)Ethyl 2-methylbutanoate (d) Ethyl 2,2-dimethylpropanoate
Which, if any, of the following compounds can be prepared by an acetoacetic ester synthesis? Explain.

Heating carvone with aqueous sulfuric acid converts it into carvacrol. Propose a mechanism for the isomerization.

How would you synthesize the following compounds from cyclohexanone?
More than one step may be required.

One way to determine the number of acidic hydrogens in a molecule is to treat the compound with NaOD in D2O, isolate the product, and determine its molecular weight by mass spectrometry. For example, if cyclohexanone is treated with NaOD in D2O, the product has MW =102. Explain how this method works.
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